Raise your hand if you dread the bi-annual seasonal wardrobe swap? Yeah, I thought so. Even me, organizer by trade who loves to sort, toss, fold, tidy… even I dread it. There is something about having to look almost every article of clothing square in the eye and acknowledge its existence that is a little bit daunting. Because, let’s face it, none of us have our wardrobe completely under control (if you do, I applaud you… and you needn’t read further).

If you read about the “proper” way to conduct the seasonal wardrobe swap, there will be info about trying things on before you pack them away, laundering your clothes, storing it in air-tight containers, etc. You know all of this. So instead, I thought I’d share the things that I tell myself every time I tackle this project (because yes, even us organizers struggle with making decisions about our stuff!)…

Be honest with yourself! You know yourself best. Are you someone who is going to take things to get tailored? Are you really going to spend the time on the red wine stain you got on your favorite blazer last winter? Do you really go out often enough to warrant a dozen fun, dressy tops? If the answers are yes, then by all means, keep that stuff! But, for many of us, it’s easy to fool ourselves about our behaviors. For example, I have (well, had) a maxi dress that I bought three summers ago. The top didn’t fit me right, but it was cute, comfortable and on sale (winning combo!) so I grabbed it and thought I’d just have it taken in. Well, apparently I’m not someone who takes things to get tailored. Last week, when putting away my summer clothes, the adorable dress went in the donation pile. If I didn’t bring it to a tailor in three years, it’s never going to happen. So embrace who you are, your habits and behaviors, and just know what is realistic for you.

Release the guilt! If you read my post about the shirt I never wore, this may sound familiar. It’s ok to acknowledge that things you once loved and adored are no longer things you would consider wearing in public. It’s ok to admit that something expensive was a bad purchase. It’s ok to say goodbye to your ill-fitting college sweatpants or a sentimental t-shirt once it has served you well (or even if it hasn’t). I hung on to a pair of mittens that my sister knit for me many years ago because the gesture was so sweet. They itch and I never, ever wore them. I finally decided that perhaps someone else could use warm hands and put them in my donation pile. When I sheepishly admitted this to my sister her response was “What mittens?” No guilt needed. They are, after all, just clothes.

Clothes should feel good! Speaking of itchy gloves, I firmly believe that life is too short to wear anything that itches. Or falls down. Or rides up. Of course we all have a few pairs of heels that make our feet scream or dresses that don’t allow for a deep breath – that’s just part of life, right? I’m talking about the clothes you wear every day. What you work, lounge, sleep, exercise and grocery shop in. That stuff should feel good on two levels; it should be fairly comfortable and you should like how you feel in it. Sounds obvious, I know. But when you take an extra second to really think about how you feel when you put something on, you may realize that you’ve been overlooking a flaw in function or comfort that has been subtly driving you crazy. I have a shirt with a pocket and a hood that I tend to put on in the evenings when I’m ready to get comfy. The wrists are cinched and have no give, so they can’t be pushed back. It wasn’t until writing this post that I’ve come to terms with the fact that the darn sleeves get soaking wet every time I do the dishes or give my kids a bath – things I do every single time I have the thing on! Wet sleeves = uncomfortable = time for it to go!

So, yes, the dreaded wardrobe switch-a-roo may be a tedious and slightly painful process. But, if you look at is an opportunity to clean out and simplify, to be honest with yourself, to make decisions guilt-free, and to make sure your wardrobe contains mainly things that make you feel good, I promise you’ll like the results. And just think, when you get rid of the stuff that isn’t serving you well, you won’t have to worry about where to put a few new purchases for the season. It’s a win-win!